DE60003567T2 - COMBATING SOIL INSECTS WITH PHENYLPYRAZOLENE - Google Patents

Description

The present invention relates new compositions to combat of soil insects in their different forms of development, in particular compositions which are suitable for the control of fast beetles. The invention also relates to a method using these compositions become.

In particular from the patent applications EP 295117 , WO 87/3781, 93/6089, 94/21606 are insecticidal Phenylpyrazoltyps which are suitable for the control of insects known. In the patent applications EP 295117 and 836386 Also mentioned are compositions containing 0.01% to 5% of these active ingredients.

Japanese Patent Application No. Hei. 08-175910 describes a poison bait for the fight of ants, fipronil as an insecticidally active substance and one for such Bait usual Carrier, for example, on cereal, sugar, oil, animal matter, flavoring, Binder, solvent, Gelling agent and optionally preservative or antioxidant base contains. An example of such a bait is described; he contains 0.01 parts fipronil, 30 parts wheat flour, 20 parts doll powder, 10 parts of peanut oil, 20 parts Powdered sugar and 19.99 parts dextrin.

Published under No. 97/04654 (D2) International patent application relates to combinations of insecticides Oxime carbamate type compounds such as aldicarb or aldoxycarb, with compounds having a pyrazole, pyrrole or phenylpyrazole group, and agrichemical compositions containing such combinations contain. These compositions are described very generally and it will not be a bait another carrier mentioned on vegetable meal basis.

The document with the file number XP-002135101 refers to a study that shows the effectiveness of Attractant baits, which consist of different flours, but no insecticide active ingredient have concerns. This investigation extended over several Months to the number fast-beetle to count at a certain place. The baits, The best results were with water moistened and then covered with a sheet of polyethylene and were three weeks long used in the month of April of the evaluation year.

Document XP-002135103 describes an insecticidal bait for fighting of owls of the species Prodenia litura, of 5 parts of an insecticide Composition, namely 1-naphthyl-N-methylcarbamate, also called carbaryl, 29 parts of rice bran, 29 parts flour, 6 parts molasses, 35.5 parts chalk and 0.5 parts Contains CM-cellulose.

The document XP-002135105 describes a poison bait in the form of tablets containing 0.01 to 2% of a compound at which it is an analog of the insect juvenile hormone or one Insect chitin formation inhibitor, microcrystalline cellulose and cereal flour and 0.1 to 10% by weight of vegetable oil and 10 contains up to 40% by weight of sugar. This bait is for the fight of cockroaches, ants and carabidae.

U.S. Patent No. 4,834,977 a poison bait, which consists essentially of at least one insecticidal compound from the Group of compounds of the organophosphorus, carbamate and pyrethroid type contains and using a traditional film former material as well as microcrystalline Cellulose and powders of plant products is encapsulated.

Document XP-002135104 reports a Efficacy study of different insecticides that respond to different Way to control maize crops click beetles were applied. In this document, the use of food baits without any insecticidal active ingredient for the numerical determination of fast-beetle populations indicated, but without any Information is given regarding the composition of these food baits become.

The fast-beetles are one Family of insects responsible for certain crops, in particular for maize, sugar beet, sunflower, Potato and rape cultures, are particularly harmful. Their harmfulness is particularly pronounced insofar as caterpillars of the fast beetles over a long period, namely up to 5 years, can remain in the ground.

Although bait for different insect species and feeding formulations have been proposed, these formulations are not always for all insect species effective, and it must insecticidal forms or formulations are found which are particularly effective for various applications, in particular for the control of fast beetles, are.

What the insecticides on or applied in the soil, it is still desirable to To find conditions and formulations with which as possible low dosages good efficacy can be achieved.

An object of the invention is to overcome these difficulties in whole or in part.

Another object of the invention is in it, connections that for the fight insects that are not sociable, beneficial and effective are to propose.

Another object of the invention is to provide compositions useful for the control of Bo Insects, especially fast beetles, especially fast beetles in the caterpillar stage, are beneficial and effective to propose.

Another object of the invention is therein, compositions containing at least one insecticidally active phenylpyrazole-type and conveniently on or in the soil can be applied provide.

Another object of the invention is in it, insecticidal compositions, despite low application rates are powerful, to propose.

It has now been found that these Targets in whole or in part by means of the compositions according to the invention and the control method according to the invention, which are described in detail in the following text could be achieved. It should be noted that it Unless otherwise stated, at the percentages indicated in the present text Weight percent is.

• a) 0,001 bis 5%, vorzugsweise 0,05 bis 1%, noch stärker bevorzugt 0,05 bis 0,5%, einer Verbindung der Formel (I)
  
  in der R₁ ein Halogenatom oder eine CN-Gruppe, eine Methylgruppe oder eine CH₃CO-Gruppe bedeutet, R₂ S(O)_nR₃ bedeutet, R₃ Alkyl oder Halogenalkyl bedeutet, R₄ ein Wasserstoff- oder Halogenatom oder einen NR₅R₆-, S(O)_mR₇-, C(O)R₇- oder C(O)O-R₇-Rest, Alkyl, Halogenalkyl oder OR₈ oder einen -N=C(R₉)(R₁₀)-Rest darstellt, R₅ und R₆ unabhängig das Wasserstoffatom oder einen Alkyl-, Halogenalkyl-, C(O)Alkyl- oder S(O)_rCF₃-Rest darstellen, oder R₅ und R₆ gemeinsam einen zweiwertigen Alkylenrest, der von ein oder zwei zweiwertigen Heteroatomen wie Sauerstoff oder Schwefel unterbrochen sein kann, bilden können, R₇ einen Alkyl- oder Halogenalkylrest darstellt, R₈ einen Alkyl- oder Halogenalkylrest oder ein Wasserstoffatom darstellt, R₉ einen Alkylrest oder ein Wasserstoffatom darstellt, R₁₀ eine Phenyl- oder Heteroarylgruppe, die gegebenenfalls durch ein oder mehrere Halogenatome oder Gruppen wie OH, -O-Alkyl, -S-Alkyl, Cyan oder Alkyl substituiert sein kann, darstellt, X ein dreiwertiges Stickstoffatom oder einen C-R₁₂-Rest darstellt, wobei die drei anderen Valenzen des Kohlenstoffatoms Bestandteil des aromatischen Rings sind, R₁₁ und R₁₂ unabhängig voneinander ein Wasserstoff- oder Halogenatom darstellen, R₁₃ ein Halogenatom oder eine Halogenalkyl-, Halogenalkoxy-, S(O)_qCF₃ oder SF₅-Gruppe darstellt, m, n, q, r unabhängig voneinander eine ganze Zahl 0, 1 oder 2 darstellen, unter der Bedingung daß, wenn R₁ Methyl bedeutet, R₃ Halogenalkyl, R₄ NH₂, R₁₁ Cl, R₁₃ CF₃ und X N bedeuten,
• b) 0, 05 bis 10%, vorzugsweise 0, 1 bis 5%, eines (oder mehrerer) Feuchthaltemittel, vorzugsweise eines organischen Feuchthaltemittels, sowie
• c) 40 bis 99%, vorzugsweise 50 bis 98% (stärker bevorzugt 70 bis 97%), eines pflanzlichen Mehls.

The present invention therefore primarily relates to insecticidal compositions comprising:

• a) from 0.001 to 5%, preferably from 0.05 to 1%, even more preferably from 0.05 to 0.5%, of a compound of the formula (I)
  
  in which R _{1 is} a halogen atom or a CN group, a methyl group or a CH ₃ CO group, R _{2 is} S (O) _n R ₃ , R _{3 is} alkyl or haloalkyl, R _{4 is} a hydrogen or halogen atom or a NR ₅ R ₆ -, S (O) _m R ₇ -, C (O) R ₇ - or C (O) OR ₇ radical, alkyl, haloalkyl or OR ₈ or a -N = C (R ₉ ) (R ₁₀ ) radical, R ₅ and R ₆ independently represent the hydrogen atom or an alkyl, haloalkyl, C (O) alkyl or S (O) _r CF ₃ radical, or R ₅ and R ₆ together represent a divalent alkylene radical which may be interrupted by one or two divalent heteroatoms such as oxygen or sulfur, R _{7 represents} an alkyl or haloalkyl radical, R _{8 represents} an alkyl or haloalkyl radical or a hydrogen atom, R _{9 represents} an alkyl radical or a hydrogen atom, R _{10 is} a phenyl or heteroaryl group which may optionally be substituted by one or more halogen atoms or groups such as OH, -O-alkyl, -S-alkyl, cyano or alkyl kan n, X represents a trivalent nitrogen atom or a CR ₁₂ radical, the other three valences of the carbon atom being part of the aromatic ring, R ₁₁ and R ₁₂ independently of one another representing a hydrogen or halogen atom, R ₁₃ a halogen atom or a haloalkyl -, haloalkoxy, S (O) _q CF ₃ or SF ₅ group, m, n, q, r independently represent an integer 0, 1 or 2, under the condition that when R _{1 is} methyl, R ₃ haloalkyl, R _{4 is} NH ₂ , R _{11 is} Cl, R _{13 is} CF ₃ and X is N,
• b) 0, 05 to 10%, preferably 0, 1 to 5%, of one (or more) humectants, preferably an organic humectant, as well as
• c) 40 to 99%, preferably 50 to 98% (more preferably 70 to 97%) of a vegetable flour.

The alkyl radicals of the definition of the formula (I) generally contain 1 to 6 carbon atoms. The ring formed by the divalent alkylene radical, R ₅ and R ₆ , as well as the nitrogen atom to which R ₅ and R _{6 are} bonded, is generally a ring of 5, 6 or 7 ring members ,

The compound of the formula (I) may be prepared according to one of the patent applications WO 87/3781, 93/6089, 94/21606 or US Pat EP 295117 or any other method familiar to those skilled in the art of chemical synthesis. In the present text This compound is also referred to by the term active ingredient.

Among the vegetable flours that can be used Flours are called by grinding cereal grains like Wheat, barley, rye, triticale, oats or even rice, sorghum, Soy or maize, preferably the flour is a flour based on corn. A mixture of such vegetable Flour is also provided in the invention.

Among the organic humectants are the hydrophilic macromolecular derivatives of plant origin, in particular the hydrophilic cellulose derivatives, especially cellulose, to call, but also one or more explosives. The usage These compounds may be particularly advantageous if granules of flours such as durum wheat flour are used. To the Counting explosives Strength, sodium carboxymethyl starch, Cellulose such as microcrystalline cellulose, modified celluloses such as sodium carboxymethylcellulose, bentonite, aluminum silicate and Magnesium silicate, sodium polynaphthalenesulfonate, sodium dodecylbenzenesulfonate, Sodium dioctylsulfosuccinate, lignosulfonate, a saccharide derivative such as lactose, fructose, sucrose, mannitol or dextrose, or a crosslinked polyvinylpyrrolidone derivative. If you use a disintegrant, so the composition of the invention 0.5 to 30 wt .-%, preferably 1 to 20 wt .-%, of this or this Contain means in terms of dry matter.

According to a variant of the composition according to the invention contains the composition 3 to 30%, preferably 4 to 20%, of sugars. The sugars are in particular from the group of mono-, oligo- or Polyorganosaccharides, especially from the group of sucrose, lactose, Fructose, dextrose, glucose, or even molasses or honey selected.

The compositions according to the invention can also be Preservative that prevents and eliminates the breakdown of flours the group sodium benzoate, 1,2-benzisothiazolin-3-one, Benzoic acid, para-hydroxybenzoic acid and their derivatives, esters and alkali or alkaline earth salts, in particular the sodium salt, 2-phenylphenol and its alkali or alkaline earth salts, especially the sodium salt, as well as paranitrophenol is selected, contain.

Other additives such as dyes or attractants for the pests or repellants for Birds or beneficials or to be protected Animals can Also included.

There may be other formulants such as adhesives, agglomerating agents, feeding agents, agglutinating agents, Gelling agent, propellant, anti-adhesive agent and the like used become.

A preferred group of compounds of the formula (I) comprises the compounds in which R _{1 is} CN and / or R _{3 is} haloalkyl and / or R _{4 is} NH ₂ and / or R ₁₁ and R _{12 are,} independently of one another, a halogen atom and / or R _{13 is} haloalkyl mean.

According to a particularly advantageous Variant of the invention is used in the invention Compound of the formula (I) for 5-amino-3-cyano-1- [2,6-dichloro-4- (trifluoromethyl) phenyl] -4 - [(trifluoromethyl) sulfinyl] -1H-pyrazole, which is referred to in the examples with fipronil.

The formulations of the invention are in general in the form of granules. The granule size is advantageously between 0.1 mm and 3 cm, preferably between 0.5 and 4 mm. This granulate is advantageously water-insoluble (insofar when it is resistant to decomposition in water).

The compositions of the present invention may be prepared by simply mixing the various ingredients, preferably by cold or hot extrusion or compression, into any of the granulation or coating techniques known per se. For the preparation of such granules, it is easy to use, for example, under the no. EP 0575838 Published European patent application and / or other techniques, for example, extrusion, with which the skilled person is familiar.

The invention also relates to a method to protect crops against insects, especially beetles, by doing so characterized in that an effective amount of a composition in the form of granules with a size of 0.2 mm to 2 cm, containing one active ingredient from the group of products of the formula I, imidacloprid, acetamiprid, nitenpyram and thiamethoxam or in the soil (preferably in the soil) of the to be cultivated surface comprises applying. The products of formula I are preferred.

The invention therefore relates entirely especially a method of protecting cereal crops, preferably Maize crops, or sugar beets, Sunflower, potato or rape cultures. The formulations according to the invention be beneficial before sowing this culture or simultaneously applied with sowing.

The invention also relates a method of control of insects, especially of beetles, characterized that he an effective amount of one of the compositions of the invention on or in the soil (preferably in the soil) where these insects are can be or are located comprises applying.

As effective amount one uses often Amount of composition, the application rate of 1 to 50 g / ha, preferably 3 to 40 g / ha corresponding to compound of formula (I).

A special feature of the method according to the invention for fighting of insects is that one on or in the soil a composition with an application rate, the no deadly contact effect, but a deadly one ate effect causes, brings.

In other words, the process is special at the fast beetles in that one the fast-beetle by applying an application rate that does not have a lethal contact effect, but a deadly one ate effect causes, kills. A theory for the good effectiveness of the treatment method according to the invention, at which is the application rates of in particular the compounds of the formula I can greatly reduce, based on the fact that when the bait according to the invention for Death of a fast-beetle guided This, in turn, has itself as bait for other fast beetles that therefore also eat an insecticide-containing product (the dead beetle), can serve.

In connection with the present Text are the terms insecticide / insecticide and insect in the broad sense and not strictly scientific (zoological) meaning. Under the term insect Therefore, one understands every very small animal, such as arthropods (insects in the narrow zoological sense, Arachnida, Myriapoda) as well as nematodes.

As soil insects against which the Invention is particularly effective, for example, the following call:

• – Diplopoda,
• – Tausendfüßler.

Coleoptera (wireworms (Agriotes spp.), Eleodes species, "white grubs") such as:
Agriotes lineatus (field humus beetle, Elateridae),
Agriotes sordidus (Elateridae),
Agriotes obscurus (Dusky Humus Fast Beetle, Elateridae),
Agriotes sputator (Garden humus fast-beetle, Elateridae),
Athous spp. (Elateridae),
Atomaria linearis (Cryptophagidae),
Melolontha spp. (Grubs, Scarabaeidae),
Bothynoderes,
Limonius spp. (US-beetle)
Melanotus spp. (US-beetle)
Diabrotica spp. ("Corn rootworms", Crysomelidae),
Tanymecus palliatus (Spitzsteuckiger Rübenrüßler, Curculionidae),
Lepidoptera (owls) like:
Autographa spp., Mamestra spp., Agrotis spp. ("Cutworms", "vers gris"), Euxoa spp. ("cutworms", "vers gris"), Spodoptera spp. (Spodoptera exigua, Spodoptera littoralis),
Diptera (like Tipula spp.),
Myriapods:

• - Diplopoda,
• - centipede.

Below the ground bugs, against the invention is particularly effective are Agriotes spp., Athous spp. and Limonius spp. to call.

The granules of the invention is advantageously placed in the ground at a depth of 1 to 5 cm.

The compositions of the invention are insofar particularly advantageous, as one thereby lower drug application rates as with similar ones can use known compositions.

The following examples illustrate the Invention, however, are not limiting. In these examples if the compound of the formula (I) used is Fipronil.

Example 1:

An area of 0.1 ha is ordered with corn, with approximately 8000 untreated grains. This area is divided into 40-m ² -Parzellen.

At the same time as the seed, a 2 mm granulate, which is composed as follows, is incorporated into the seed furrow in the soil: 0.25% fipronil, 93.5% Corn flour, 2% cellulose, 4% lactose, 0.2% Para nitrophenol, 0.05% Pigment Blue 15.3.

The amount of granules thus applied is in the range of 2.5 to 10 kg per hectare. Plots are left untreated to serve as controls and to determine the extent of damage caused by the insects. Likewise, plots with an allegedly effective commercially available In treated as a kind of reference. Each test member is repeated four times.

About 20 days after sowing the accumulated corn plants are counted.

Observed at ST Hilaire (30) one 22 days after sowing in the furrow of 4 untreated plots 19 plants per 10 meters furrow. In the invention with a Fipronil application rate of 6 g per hectare of treated plots was observed 49 plants per 10 meters furrow.

At a fipronil application rate of 12.5 g per hectare are observed 48 to 50.5 plants per 10 meters Furrow.

At a fipronil application rate of 25 g per hectare are observed from 45.5 to 51.3 plants per 10 meters Furrow.

At a fipronil application rate of 50 g per hectare are observed 49 plants per 10 meters furrow.

To the same result with a To obtain traditional granules (clay-based) must be 200 g fipronil per hectare.

The soil is dug up and scratched, around the for the damages catch and determine responsible insects; at the untreated Control is a strong occurrence of fast-beetle larvae of the genus Agriotes, in particular Agriotes sordidus.

Example 2:

An area of 1 ha is ordered with corn, with approximately 98100 untreated grains. This area is divided into 27-m ² -Parzellen.

At the same time as the seed, a 2 mm granulate, which is composed as follows, is incorporated into the seed furrow in the soil: 0.25% fipronil, 93.5% Corn flour, 2% cellulose, 4% lactose, 0.2% Para nitrophenol, 0.05% Pigment Blue 15.3.

The granulated amount thus applied is in the range of 2.5 to 10 kg per hectare. There are parcels left untreated to serve as a control and to measure the extent of damage caused to the insects. Likewise are parcels treated with an allegedly effective commercially available insecticide and referred to as reference plots. Each test subject becomes repeated four times.

About 50 days after sowing the accumulated corn plants are counted.

Observed at the Beaufort site (62) one 50 days after sowing in the furrow of 4 untreated plots 30 plants per 10 meters furrow. In the invention with a Fipronil application rate of 6 g per hectare of treated plots was observed 40 plants per 10 meters furrow.

At a fipronil application rate of 12.5 g per hectare are observed from 43 to 46 plants per 10 meters Furrow.

At a fipronil application rate of 25 g per hectare, 44.5 to 50 plants are observed per 10 meters Furrow.

At a fipronil application rate of At 50 g per hectare, 49.8 plants are observed per 10 meters furrow.

To the same result (52 plants per 10 meters) with a traditional granules (clay-based) too have to achieve 200 g of fipronil are applied per hectare.

The soil is dug up and scratched, around the for the damages catch and determine responsible insects; at the untreated Control is a strong occurrence of fast-beetle larvae the genus Agriotes, in particular Agriotes lineatus observed.

Example 3: Experiments for Effectiveness of bait granules according to the invention in potato cultures.

At the same time as the seed, a granulate according to the invention, which is composed as follows, is incorporated into the seed furrow in the soil: 12.5 g / kg Fipronil (using a 500 g / l fipronil SC), 945.5 g / kg a) cornmeal (granules A) or b) rice flour (granules B), 40 g / kg lactose, 2 g / kg Paranitrophenol.

It is the effectiveness of the above two granules A and B, which are used at rates of 5 and 2.5 g fipronil per hectare, and the same fipronil, which was applied by spraying in application rates of 50 and 25 g / ha (under use of Regent ^® 800WG) (compound C), against Agriotes (click beetles) compared 90 days after the sowing.

You get to the following results the number of holes per 10 knots (= N) can be specified:

This result clearly shows the good control result against beetle, which was achieved with the granules according to the invention, which led to the same result as Regent ^® 800WG, but with a reduced by a factor of 10 application rate.

Claims (17)

Insecticidal compositions comprising: a) from 0.001 to 5%, preferably from 0.05 to 1%, even more preferably from 0.05 to 0.5%, of a compound of the formula (I)

in which R _{1 is} a halogen atom or a CN group, a methyl group or a CH ₃ CO group, R _{2 is} S (O) _n R ₃ , R _{3 is} alkyl or haloalkyl, R _{4 is} a hydrogen or halogen atom or a NR ₅ R ₆ -, S (O) _m R ₇ -, C (O) R ₇ - or C (O) OR ₇ radical, alkyl, haloalkyl or OR ₈ or a -N = C (R ₉ ) (R ₁₀ ) radical, R ₅ and R ₆ independently represent the hydrogen atom or an alkyl, haloalkyl, C (O) alkyl or S (O) _r CF ₃ radical, or R ₅ and R ₆ together represent a divalent alkylene radical which may be interrupted by one or two divalent heteroatoms such as oxygen or sulfur, R _{7 represents} an alkyl or haloalkyl radical, R _{8 represents} an alkyl or haloalkyl radical or a hydrogen atom, R _{9 represents} an alkyl radical or a hydrogen atom, R _{10 is} a phenyl or heteroaryl group which may optionally be substituted by one or more halogen atoms or groups such as OH, -O-alkyl, -S-alkyl, cyano or alkyl kan n, X represents a trivalent nitrogen atom or a CR ₁₂ radical, the other three valences of the carbon atom being part of the aromatic ring, R ₁₁ and R ₁₂ independently of one another representing a hydrogen or halogen atom, R ₁₃ a halogen atom or a haloalkyl -, haloalkoxy, S (O) _q CF ₃ or SF ₅ - group, m, N, q, r independently represent an integer 0, 1 or 2, under the condition that when R _{1 is} methyl, R ₃ haloalkyl, R _{4 is} NH ₂ , R _{11 is} Cl, R _{13 is} CF ₃ and X is N, b) 0.05 to 10%, preferably 0.1 to 5%, of one (or more) humectants, preferably an organic humectant, and c) 40 to 99%, preferably 50 to 98% (more preferably 70 to 97%) , a vegetable flour. Insecticidal compositions according to claim 1, characterized characterized in that Flours by grinding cereal grains such as wheat, barley, rye, triticale, oats or even rice, sorghum, Soy or corn can be obtained. Insecticidal compositions according to claim 1 or 2, characterized in that it the flour is cornmeal. Insecticidal compositions according to any one of claims 1 to 3, characterized in that under the organic humectants the hydrophilic macromolecular Derivatives of plant origin, in particular the hydrophilic cellulose derivatives, especially cellulose, to name a few. Insecticidal compositions according to any one of claims 1 to 4, characterized in that the composition 3-30% preferably 4-20%, Contains sugars. Insecticidal compositions according to any one of claims 1 to 4, characterized in that the sugars in particular from the group of mono-, oligo- or polyorganosaccharides, especially from the group sucrose, lactose, fructose, dextrose, Glucose, or molasses or honey are selected. Insecticidal compositions according to any one of claims 1 to 6, characterized in that it also a Preservative that prevents and eliminates the breakdown of flours the group of sodium benzoate, 1,2-benzisothiazolin-3-one, benzoic acid, para-hydroxybenzoic acid and their derivatives, esters and alkali or alkaline earth salts, in particular the sodium salt, 2-phenylphenol and its alkali or alkaline earth salts, especially the sodium salt, as well as paranitrophenol is selected, contain. Insecticidal compositions according to any one of claims 1 to 7, characterized in that they further Additives such as dyes or attractants for the pests or repellents for birds or beneficials or to be protected Animals and / or other formulation materials such as adhesives, agglomerating agents, ate promoting Agents, agglutinants, gelling agents, propellants, non-stick agents and the like. Insecticidal compositions according to any one of claims 1 to 8, characterized in that it is in the compound of formula (I), 5-amino-3-cyano-1- (2,6-dichloro-4- (trifluoromethyl) phenyl] -4 - [(trifluoromethyl) sulfinyl] -1h-pyrazole is. Insecticidal compositions according to any one of claims 1 to 9, characterized in that the formulations according to the invention in the form of granules, the granule size advantageously between 0.1 mm and 3 cm, preferably between 0.5 and 4 mm and that Granules advantageously water-insoluble. Method for controlling insects, thereby characterized in that an effective amount of a composition according to any one of claims 1 to 10 in the form of granules with a size between 0.2 mm and 2 cm on or in the soil (preferably in the soil) of the to be cultivated surface comprises applying. A method of protecting crops according to claim 11, characterized in that a compound of formula I used. Method according to claim 11 or 12, characterized that he Cereal crops, preferably maize crops, or sugar beet, sunflower, Protects potato or rape cultures. Method according to one of claims 11 to 13, characterized that he to combat Insects, especially of beetles, an effective amount of the compositions of the invention comprises applying. Method according to one of claims 12 to 14, characterized that the effective amount of composition of an application rate of 1 to 50 g / ha, preferably 3 to 40 g / ha, of the compound of the formula (I) equivalent. Method for controlling insects after claims 11-15 when you get on or in the ground a composition with a Application rate, which is not deadly Contact, but a lethal feeding effect causes, brings. Method according to claim 16 against fast beetles.